Vacation rentals with a pool in New Haven

4.95 out of 5 average rating, 177 reviews

Cottage in Guilford

Luxury cottage by the sea with hot tub and pool

Jennifer And JonRating, 5 stars3 months ago

We loved this airbnb and stayed for 3 weeks. It sits right on the edge of the marsh with an extraordinary view. We greatly enjoyed how a short walk away is Chaffinch Island, which is a gorgeous park full of tides pools and hackberry trees. The space was clean and comfortable and Mary was a fantastic host. You can see a lighthouse on an island 3 miles out sea from all the rooms, even the main bed.

5 out of 5 average rating, 22 reviews

Home in Roxbury

Zoom Map 5* Town Roxbury! "Tophet Pool" PoshPadsCT

AllanRating, 5 stars19 months ago

Beautiful home, exactly how it was described and looked even better in person. Incredible surrounding areas and activities. Steven was helpful throughout the stay and incredibly flexible. Wonderful host! Will definitely be planning a yearly visit.

4.93 out of 5 average rating, 318 reviews

Guesthouse in Southbury

Charming Guest Cottage with Modern Amenities

CarolineRating, 5 stars3 months ago

John’s place was the perfect respite for our multi-day stay! The clean and cozy space is perfectly situated close to trails and parks for our Australian shepherd, but only a short drive to all the shopping you’d need (e. g. ShopRite for groceries and necessities). We thoroughly enjoyed our stay and know you will too!

4.97 out of 5 average rating, 200 reviews

Home in Monroe

Garden Level Suite with Beautiful Pool

GraceRating, 5 stars2 months ago

We had an amazing time at Marybeth’s suite—it truly felt like a winter wonderland. Our kids had a blast "swimming" in the snow and "rolling" over the gentle hills. Every moment was filled with joy, whether we were relaxing in the sunroom, playing in the snow, or swinging outside. The time spent together as a family, along with our conversations with Marybeth and her family, was truly precious. We can’t wait to return in the summer!

4.93 out of 5 average rating, 80 reviews

Home in Redding

Lovely Country Retreat:

BridgetRating, 5 stars3 months ago

We spent Christmas at Gaels home. It was so fun! The home is beautiful. It was very roomy for our family. The neighborhood was quiet and felt very safe. We were able to relax and enjoy ourselves. The kitchen had everything needed to prepare meals. We really enjoyed our stay. I highly recommend this beautiful home!

4.84 out of 5 average rating, 101 reviews

Guesthouse in Easton

Entire Guest House at Fox Pond Farm.

LucyRating, 5 stars8 months ago

Stayed at Scott and Durelle's guest house for my 30th birthday with 10 friends. Booked mostly for the pool to enjoy a hot August weekend, but unfortunately there was a huge tropical storm! We still enjoyed the spacious house, jumping into the pool in the rain, cooking on the grill in a moment of dry weather, and overall had a peaceful and fun weekend despite crazy weather! A testament to this great property - which is beautiful and just as in pictures.

5 out of 5 average rating, 17 reviews

Home in Roxbury

Bright Mid-Century Modern Retreat-90 min from NYC

SidRating, 5 stars2 months ago

My family and I had a wonderful weekend at the house. The house is beautiful and was extremely clean when we arrived. Luiz kindly left a sled for my kids to use in the yard. There is plenty of outdoor space and the yard has a good deal of privacy. There are two bedrooms and a den/office with a TV. The kitchen has everything we needed. Luiz was very easy to communicate with.

4.97 out of 5 average rating, 145 reviews

Home in North Fork

Secluded Farmhouse - Studio Apartment Style Unit

JamieRating, 5 stars2 weeks ago

We had a great stay at Jess and Zack’s place for my birthday weekend on the North Fork! They provided clear directions ahead of time on how to find their place and how to check in. We were greeted by the sweetest pup. The space was spotless and very comfortable. We had a fire in the fire pit one night and that was excellent. It’s super close to lots of great restaurants and wineries! I would recommend their place to anyone looking for a quiet and peaceful getaway!

5 out of 5 average rating, 14 reviews

Home in Branford

Breathtaking Panoramic Waterfront

JenRating, 5 stars1 month ago

Karen’s Branford property was fantastic for our group of 11 friends. Unbeatable views from multiple wrap around decks and many windows. Multiple spaces for gathering and a wonderful kitchen for cooking. We truly had a great stay and would happily return.

4.96 out of 5 average rating, 157 reviews

Guest suite in Guilford

Bright, Cozy Apartment in Guilford

KarenRating, 5 stars6 months ago

The home was absolutely gorgeous and peaceful. It's exactly as described but even more spacious than I expected. They put a lot into making guests feel welcome, including prompt communication, a quick walk through to explain where things are, numerous suggestions for the surrounding area, and even a tray of welcome cookies! I came for a 50k trail race, so the hot tub was a perfect added bonus. I HIGHLY suggest booking this property, and I'll definitely be back to spend some time at the beach.

0 of 0 items showing

What guests are saying

Romantic hideaway. lovely views.

5 out of 5 average rating, 7 reviews108 months ago

Overall just wow. Ginny is a warm and lovely host who communicated throughout including specifics on how to arrive, find the correct drive way (its a bit tucked away) etc. Upon arrival we were blown away by the lush greenery. Soon after we were met by Ginny who walked us through how to work the water heater for the pool and the house ac's and then she just left us to enjoy on our own. The house itself is immaculate & beautifully decorated with an attention to detail that is beyond thoughtful. The kitchen has every possible tool for cooking, the bathroom had toiletries etc. - there was nothing we could think of that we could need. We were blessed with 80+ degree weather and spent most of the time in the pool which is simply divine, floating on our backs and listening to the birds was a huge highlight. Ginny, thank you for the wonderful experience and we hope to be back soon!

Home in Newtown

What guests are saying

Shoreline Carriage House

5 out of 5 average rating, 65 reviews6 months ago

Staying with Phil and Hope was a magical time. The place is truly special and they have put so much love and care into every little detail. We stayed for over a month and felt right at home. The pool is super. As is the surrounding area; we greatly enjoyed the beach walks, stunning sunsets, cooking at home, relaxing on the porch while watching the wildlife. The carriage house is charming and offers all the amenities plus more (games, beach towels, books, cosy blankets, beautiful art etc). In walking distance you will find a terrific fish market and some excellent restaurants - we cooked fish at home at least twice a week! We had such a hard time leaving this little paradise and can’t wait to return!

Loft in Branford

What guests are saying

The Pond Mill Retreat w/ 2 Bdrms & Pool

4.98 out of 5 average rating, 94 reviews2 weeks ago

Thank you Bob and Dawn for allowing us to stay at this beautiful apartment and allowing us access to your amazing back yard with the gardens, pond and waterfall. This is the third time we've stayed here, it is our "go to place " when we visit family in Milford. Cooper, their dog, is adorable:)

Apartment in Milford

What guests are saying

Beach Area Home with Pool

5 out of 5 average rating, 5 reviews3 months ago

We loved our stay at Amy's place! The house was a great size for our family of 3 (2 adults and 1 infant) and it came with everything that we could need to relax for a few days. It was the perfect distance between the beach and the town, so we were able to get out and take a few walks. The beds were really comfortable, the water pressure in the shower was a dream and the kitchen was stocked with everything that we could possibly need to host my family for the holidays. We really appreciated how responsive and helpful Amy was as well. She was accommodating to lend us gear for our infant and to help us navigate our stay. Overall, great amenities, charming spot in town and an amazing house. Highly recommend and wouldn't hesitate to return!

Home in Fairfield

What guests are saying

Classic Red Barn with game room

4.97 out of 5 average rating, 39 reviews2 months ago

This was the second time I stayed at Vicki's gorgeous place. Vicki's is 8 minutes from my sister's house and if all goes well I will always stay at Vicki's when I am visiting as it's such a lovely place and so convenient while giving me and my partner the privacy we want when visiting extended family. Vicki's apartment is cozy and extremely clean and beautifully decorated in a modern/country style that I love.

Barn in Roxbury

What guests are saying

Cozy water view in-law private apartment 2bd/1ba

4.95 out of 5 average rating, 22 reviews3 weeks ago

Due to a sudden change to our housing arrangements, we were in desperate need of a short-term stay (or long-term in the context of airbnb). Jenna's place satisfied all our needs and exceeded our expectations. The two-bedroom guest suite has a beautiful view, and she supplied everything you need. The place is comfortable and spacious. You can tell the hosts have put into a lot of thoughts into what would make the guests feel at home and convenient. We also really appreciate how helpful, responsive and kind Jenna had been to us during our stay. Highly recommend it!

Guest suite in Portland

1 of 12 pages

Vacation rentals for every style

Get the amount of space that is right for you

Villas

Luxurious estates for the ultimate escape

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Popular amenities for New Haven rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.95 out of 5 average rating, 21 reviews

Home in Fairfield

Once a Pond - time and stress slow down.

LindaRating, 5 stars2 weeks ago

This was a beautiful home to stay at for our visit to Fairfield University. It was peaceful location near the school. The house itself was gorgeous with everything we needed for our stay. Thank you.

4.91 out of 5 average rating, 11 reviews

Home in Clinton

Clinton Beach House & Cottage w/ Pool, Near Shore

HannahRating, 5 stars3 months ago

We had a group of 8 adults and 7 kids (5 and under) and the space was great for a large group! There was plenty of room for the kids to run around downstairs and the large yard was fantastic. We were there in the winter so couldn’t take advantage of the pool but we did make a trip to the local beach (5 min drive) and use the fire pit. I definitely recommend Gregory’s place for both larger groups and families! We would love to return!

4.85 out of 5 average rating, 84 reviews

Home in Woodmont

Spacious 4 bedroom, oasis with ocean views galore

CharlesRating, 5 stars1 week ago

The absolute best Air B & B we ever stayed at. Allana was a pleasure to work with. The home was spacious, and fully stocked with everything you could possibly need, and more. Fireplace, pool, enclosed porch, sun room with coffee bar, sitting room, sunken living room, dining room with tons of chairs, kitchen bar with stools, dining room bar with stools, mud room with extra refrigerator and freezer, storage space galore, closets stocked with games, linen closets with anything you might need, big bedrooms, master bedroom with en-suite bathroom, balconies to soak in the sun, crib, high chair… too much more to even list. Our family had a fabulous time; the energy in the house is so welcoming! The soft blues are soothing, and quaint beach theme accents throughout the home lend to the relaxed vibe. The rooms flow perfectly, and provided ample space for different family members to have their own area to unwind in. Steps from beach & playground, the neighborhood is perfect for a stroll.

4.95 out of 5 average rating, 40 reviews

Home in Middletown

Hot Tub and pool Home away from home

KristenRating, 5 stars3 months ago

Jan's house was a great stay with plenty of room for six adults. We loved the game room and outdoor hot tub. Instructions for the hot tub were clear and easy to follow. We'd definitely stay again!

4.93 out of 5 average rating, 81 reviews

Home in North Fork

Modern farmhouse w/ pool, beach, horses and winery

KristiRating, 5 stars1 week ago

We had such a great time at Travis’ home. Perfect location to all the wineries and good food but private enough to feel completely relaxed. We especially loved the great big yard for our dogs. Would definitely come back!

5 out of 5 average rating, 9 reviews

Home in Woodmont

Huge Family House w/Waterviews

LynnRating, 5 stars6 months ago

We had a wonderful stay! The house can accommodate large family gatherings - there were a lot of spaces for folks to spread out as well as gather. The kitchen is very well stocked. We would definitely rent again!

4.94 out of 5 average rating, 35 reviews

Home in Fairfield

Newly-Renovated, Private, 4BR Cape w/Pool

PeterRating, 5 stars7 months ago

Great home and host. Responsive to inquiries. Would recommend!